Photo by Robin/Loving Life

Canaan Holiday Rentals

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Holiday Rentals in Canaan

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (858)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is NZ$282
includes taxes & fees
11 Jun - 12 Jun
Jiminy Peak Mountain Resort
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (73)
"Expedia said they have a Sunday buffet, but they didn't."
The price is NZ$228
includes taxes & fees
6 Jun - 7 Jun
Micosta Leisure Inn
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
"The pictures simply do not do this place justice, it’s an incredible home. Our friend group was cozy all weekend! We loved the hot tub/pool, the really interesting artwork, the driving range mat and basketball hoop. Plenty of towels and kitchen supplies. The in law apartment (which we didn’t use as sadly part of our group was unable to join us) is attached to the main home and is so cute. We had a small issue upon arrival and the hosts were immediately responsive with us troubleshooting and...
Private Estate, Heated YEARROUND Outdoor Pool
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (205)
"Had an absolutely amazing time! great location, quiet, close to everything! Plenty of things to do nearby, and host left plenty of brochures to find food or activities. Only minor downer was that the oven seemed touchy"
Berkshire Village Carriage House - Super Private!!
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (97)
"Lovely chalet by the lake, we had such a relaxing stay. The place is just like on the pictures, very quiet but not far from amenities. The host are very friendly super responsive. Thanks for having us!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is NZ$440
includes taxes & fees
24 Jun - 25 Jun
Perfect Vacation Get Away - Historical New Marlborough
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
9.6 out of 10, Exceptional, (79)
"We had 4 families and grandparents all stay together for an unforgettable weekend at Bellavista. The house had enough space for us to hang out together playing charades in the great room, ping pong tournaments in the finished attic playroom, and making holiday ornaments at the large dining room table. There were also spaces to have quiet moments when you needed it...and we even enjoyed a beautiful hike at a nearby conservation area that Laurie recommended. The house was extremely clean, fully...
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
"We had a wonderful time at the Moose Lodge. It was perfect for our family. Very clean, everything we needed and the property managers were extremely communicative. Thank you!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is NZ$540
includes taxes & fees
30 Jun - 1 Jul
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (12)
"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."
Stockbridge Home, Come Experience The Berkshires!
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"
Rockspring by AvantStay | Huge Berkshires Estate
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See all available properties in Canaan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Canaan you may be interested in

Life House Berkshires
3.5 star property
9.0 out of 10, Wonderful, (253)
"Terrific renovation of two story motel. Great bedding and toiletries. Everything has a curated retro-hipster look. Spacious shower and bathroom, closet space, robes, plenty of charging outlets and a big TV, great if you use Apple. The only downside is noisy, bulky air conditioner. Be sure to ask for a ground floor room if you have a lot of luggage; second floor is accessible only by stairs. Nice outdoor seating and clubroom. We didn't take advantage of their food or bar offerings because...
The price is NZ$215
includes taxes & fees
9 Jun - 10 Jun
Life House Berkshires
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1005)
"This is our go-to spot for short trips to the Berkshires. It's on a busy road, but set back from the street, and it's convenient to everything we need. Good breakfast (better than the one I had a much more expensive hotel in NYC last week) and it's clean and comfortable. "
The price is NZ$229
includes taxes & fees
17 Jun - 18 Jun
The Yankee, Trademark Collection by Wyndham
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (890)
"Always a great HISTORIC INN "
The price is NZ$352
includes taxes & fees
17 Jun - 18 Jun
The Red Lion Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Canaan holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Canaan. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Canaan. Seeing all the best attractions is bound to make you fall in love with Canaan. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Canaan short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Canaan?

Yes, there are holiday rentals close to the most popular sights in Canaan, or you can select a more secluded option if you're looking for a relaxing stay. Canaan is known for its restaurants and coffee shops. Make sure you have time to check out the shopping and local tours during your trip.

How many holiday rentals are there in Canaan?

Choose from 15 Expedia holiday rentals in Canaan for a memorable holiday.

What’s there to see and do in Canaan?

Explore the area and family-friendly sights such as Bousquet Ski Area, or get out into nature at a spot like Queechy Lake. Hollow FIelds Reserve and Hand Hollow State Forest are other places to visit while you're in town.

What’s a holiday rental in Canaan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Canaan. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.

Recent reviews of Canaan properties
Expedia verified reviews